Reacción #2323779

Ecuación de reacción

water

triethylamine

3, 4 dihydroxybenzylamine

(4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

→

white solid

Rendimiento 54.4%

(4Z)-6-Bromo-4-{[(3,4-dihydroxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione

Rendimiento 54.4%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture is stirred for 60 min
2. 2
   FiltraciónThe precipitate is filtered
3. 3
   Lavadowashed several times with anhydrous ether
4. 4
   OtroThe crude solid is then purified by high performance liquid chromatography

Procedimiento

According to general procedure 1, an amount of 3, 4 dihydroxybenzylamine (0.596 g, 4.3 mmol), is dissolved in N,N-dimethylformamide (61 mL). 1.8 ml (12.9 mmol) of triethylamine is added followed by 1.21 g (4.3 mmol) of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione. After the mixture is stirred at room temperature for 30 min, water (5 mL) is added and the reaction mixture is stirred for 60 min. The precipitate is filtered and washed several times with anhydrous ether. The crude solid is then purified by high performance liquid chromatography to give 910 mg of a white solid. MS (ESI) m/z 389.7 (M+1).

Fuente